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32222-06-3 (Calcitriol)

1

Identification

Calcitriol Calcitriol
Name Calcitriol
Formula C27H44O3
MW 416.64
CAS No. 32222-06-3
EINECS 250-963-8
Smiles C=C1[[email protected]](C[[email protected]@H](C/C1=C/C=C2[[email protected]]3([[email protected]@](C)([[email protected]](CC3)[[email protected]@H](CCCC(C)(O)C)C)CCC/2)[H])O)O
Synonyms 1,25-Dihydroxyvitamin D3; Rocaltrol; (1R,3S,Z)-5-((E)-2-((1R,3aS,7aR)-1-((R)-6-hydroxy-6-methylheptan-2-yl)-7a-methylhexahydro-1H-inden-4(2H)-ylidene)ethylidene)-4-methylenecyclohexane-1,3-diol
InChI InChI=1S/C27H44O3/c1-18(8-6-14-26(3,4)30)23-12-13-24-20(9-7-15-27(23,24)5)10-11-21-16-22(28)17-25(29)19(21)2/h10-11,18,22-25,28-30H,2,6-9,12-17H2,1,3-5H3/b20-10+,21-11-/t18-,22-,23-,24+,25+,27-/m1/s1
2

Introduction

Calcitriol(1,25-Dihydroxyvitamin D3; Rocaltrol ) is the hormonally active form of vitamin D, Calcitriol is the active metabolite of vitamin D3 that activates the vitamin D receptor (VDR). IC50 value: Target: vitamin D receptor Calcitriol(1,25-Dihydroxyvitamin D3; Rocaltrol ) displays calcemic actions.

Background Information

Calcitriol (1α,25-Dihydroxyvitamin D3) is Active metabolite of vitamin D3 that activates the vitamin D receptor (VDR). This hormone stimulates intestinal calcium transport at a much higher rate than vitamin D3 and hydroxy D3, and is considered to represent the biologically active form of vitamin D3.The 1α,25-Dihydroxyvitamin D3 Displays calcemic actions,stimulates intestinal and renal Ca2+ absorption and regulates bone Ca2+ turnover. Exhibits antitumor activity; inhibits in vivo and in vitro ce ......by Affix Scientific
The biologically active form of Vitamin D3, which has been found to be effective in mediating intestinal calcium absorbtion and bone calcium metabolism. ......by BOC Sciences
Calcitriol is the most active metabolite of vitamin D and also a vitamin D receptor (VDR) agonist. ......by MedChemexpress Co., Ltd.
Calcitriol is the hormonally active form of vitamin D. ......by Selleck Chemicals LLC
Calcitriol is the hormonally active form of vitamin D. ......by Target Molecule Corp.
Active metabolite of vitamin D3 that activates the vitamin D receptor (VDR). Displays calcemic actions; stimulates intestinal and renal Ca2+ absorption and regulates bone Ca2+ turnover. Exhibits antitumor activity; inhibits in vivo and in vitro cell proliferation in a wide range of cells including breast, prostate, colon, skin and brain carcinomas and myeloid leukemia cells. ......by Tocris Bioscience Inc.
3

Protocol(Only for Reference)

Cell Experiment

Animal Experiment

4

Physical and Chemical Properties

Appearance:White to off-white Solid EBNumber:EB000028778

Storage condition

Up to one week at 4°C or six months at -20°C. by Affix Scientific
Desiccate at -20°C by Tocris Bioscience Inc.

Solubility

DMSO ≥83mg/mL Water <1mg/mL Ethanol ≥83mg/mL by MedChemexpress Co., Ltd.
(25°C) * In vitro DMSO 83 mg/mL (199.21 mM); Ethanol83 mg/mL (199.21 mM); Water<1 mg/mL (<1 mM) by Selleck Chemicals LLC
Soluble in DMSO and in ethanol by Tocris Bioscience Inc.
5

Mechanism and Indication

Signaling Pathways Others
Target VD/VDR
Research Area Cancer
Indications Proteinuria Psoriasis End stage renal disease Asthma
6

Clinical Information

Product Name Sponsor & Collaborators Indications Start Date End Date Phase
Calcitriol Huashan Hospital Proteinuria 2013/3/31 2015/6/30 Phase 4 Clinical
Calcitriol Galderma SA Psoriasis 2013/3/31 2015/5/1 Phase 4 Clinical
Calcitriol Seoul National University Hospital 2013/1/31 2013/3/31 Phase 4 Clinical
Calcitriol Seoul National University Hospital End stage renal disease 2012/7/31 2013/1/31 Phase 4 Clinical
Calcitriol Kantonsspital Bruderholz Asthma 2008/8/31 2010/8/31 Phase 4 Clinical
Calcitriol - No Development Reported
Calcitriol - Launched
7

Safety Data of Calcitriol

Hazard Symbols : T+,Xn,F
Risk Statements : 26/27/28-63-36/37/38-20/21/22-11
Safety Statements : 36/37/39-45-36-26-16-7
HS Code : 29061900
RTECS : FZ4645000
WGKGermany : 3
8

Spectral Information

9

Suppliers List

Company Price and Availability Country/Region
A.G. Scientific, Inc. USA
Affix Scientific 10g/USD1695(In stock);25g/USD2450(In stock) USA
Alfa Chemistry USA
BOC Sciences
Biochempartner Co., Ltd China
CHEMSCENE, LLC 2mg/USD120();5mg/USD276() USA
Hydragon Pharma Co., Ltd. China
MedChemexpress Co., Ltd. 2mg/USD120();5mg/USD276() USA
Nectar Industrial Co., Ltd. China
Pure Chemistry Scientific Inc. 5mg/USD91(In stock) USA
Selleck Chemicals LLC 2mg/USD120(In stock);5mg/USD270(In stock);10mM/1mLIn DMSO/USD500(In stock);25mg/USD1070(In stock) USA
ShangHai PuYi Chemical Co., Ltd. China
Shanghai Bocimed Pharmaceutical Co., Ltd. China
Shanghai Haoyuan Chemexpress Co., Ltd. 2mg/USD120();5mg/USD276() China
Shanghai Zhongkang Weiye Biological Science & Technology Co., Ltd. China
Sichuan Industrial Institute of Antibiotics Co., Ltd. China
Target Molecule Corp. 2mg/USD86();5mg/USD156();10mg/USD298();25mg/USD498();50mg/USD887() USA
Tocris Bioscience Inc. USA
UHN (Shanghai) Research & Development Co., Ltd. 10g/USD1240(In stock) China
Wonder Synthesis (Beijing) Science and Development Co., Ltd. China
Xi'an Fude Technology Co., Ltd. China
Zhangjiagang Sunrise Fine Chemical Co., Ltd. China
Zhejiang Esun Chemical Co., Ltd. China
10

Related Products

Other Forms of 32222-06-3

Name CAS No Formula MW
Calcitriol D6 78782-99-7 C27H38D6O3 422.67
HLCL-61 (hydrochloride) 1158279-20-9 C23H25ClN2O 380.91
Bay 41-4109 298708-81-3 C18H13ClF3N3O2 395.76
AT 130 211364-06-6 C22H22BrN3O5 488.33
Ro 41-1049 (hydrochloride) 127917-66-2 C12H13ClFN3OS 301.77
Ro 41-1049 127500-84-9 C12H12FN3OS 265.31
HLCL-61 586395-74-6 C23H24N2O 344.45
NTRC-0066-0 1817791-73-3 C33H39N7O2 565.71
LY3177833 1627696-51-8 C16H12FN5O 309.2978
eFT508 1849590-01-7 C17H20N6O2 340.3797
CPI-1205 1621862-70-1 C27H33F3N4O3 518.57
BAY-1436032 1803274-65-8 C26H30F3N3O3 489.53
eFT508 hydrochloride 1849590-02-8 C17H21ClN6O2 376.8406
Bay 41-4109 (racemate) 298708-79-9 C18H13ClF3N3O2 0.0
Bay 41-4109 (less active enantiomer) 476617-51-3 C18H13ClF3N3O2 395.76

Recommended Compounds in VD/VDR

Name CAS No Formula MW
25,26-Dihydroxyvitamin D3 29261-12-9 C27H44O3 416.64
(24R)-MC 976 112828-09-8 C27H42O3 414.62
(24S)-24,25-Dihydroxyvitamin D3 55700-58-8 C27H44O3 416.64
Calcitriol Impurities D 103656-40-2 C28H46O3 430.663
Calcifediol (monohydrate) 63283-36-3 C27H44O2 400.64
Cholecalciferol 67-97-0 C27H44O 384.64
(24S)-MC 976 112849-14-6 C27H42O3 414.62
(1S,4R,E)-4-((1R,3aS,7aR,E)-4-((Z)-2-((3S,5R)-3,5-bis((tert-butyldimethylsilyl)oxy)-2-methylenecyclohexylidene)ethylidene)-7a-methyloctahydro-1H-inden-1-yl)-1-cyclopropylpent-2-en-1-ol C39H68O3Si2 641.1264
VD3-D6 118584-54-6 C27H38D6O 390.67
VD2-D3 1217448-46-8 C28H41D3O 399.67
25-Hydroxy VD2-D6 1262843-46-8 C28H38D6O2 418.68
1alpha, 25-Dihydroxy VD2-D6 216244-04-1 C28H38D6O3 434.68
Calcipotriol (monohydrate) 147657-22-5 C27H42O4 430.62
Cholecalciferol 67-97-0 C27H44O 384.63766
Calcitriol Impurities A 73837-24-8 C27H44O3 416.6365
(1R,3S,E)-5-((E)-2-((1R,3aS,7aR)-1-((2R,5S,E)-5-cyclopropyl-5-hydroxypent-3-en-2-yl)-7a-methylhexahydro-1H-inden-4(2H)-ylidene)ethylidene)-4-methylenecyclohexane-1,3-diol 910133-70-9 C27H40O3 412.6047
Paricalcitol 131918-61-1 C27H44O3 416.64
MC 976 129831-99-8 C27H42O3 414.62
24R-Calcipotriol 112827-99-3 C27H40O3 412.6
MC 1046 126860-83-1 C27H38O3 410.59

Recommended Compounds in Same Indication

Name CAS No Formula MW
AN-2728 906673-24-3 C14H10BNO3 251.05
BMS-582949 623152-17-0 C22H26N6O2 406.48
SCH 527123 473727-83-2 C21H23N3O5 397.42
Beclometasone dipropionate 5534-09-8 C28H37ClO7 521.04
Setipiprant 866460-33-5 C24H19FN2O3 402.42
Levalbuterol (tartrate) 661464-94-4 C30H48N2O12 628.71
Bardoxolone 218600-44-3 C31H41NO4 491.66
Bardoxolone (methyl) 218600-53-4 C32H43NO4 505.69
Cinacalcet (hydrochloride) 364782-34-3 C22H23ClF3N 393.87
Sotrastaurin 425637-18-9 C25H22N6O2 438.48
OC000459 851723-84-7 C21H17FN2O2 348.37
Aleglitazar (racemate) 475479-24-4 C24H23NO5S 437.5081
Vilanterol (trifenatate) 503070-58-4 C44H49Cl2NO7 774.77
Apremilast 608141-41-9 C22H24N2O7S 460.5
Formoterol 67346-49-0 C19H24N2O4 344.40486
Talarozole 201410-53-9 C21H23N5S 377.51
Formoterol (Fumarate) 43229-80-7 0.0
Dimethyl fumarate 624-49-7 C6H8O4 144.13
Cinacalcet 226256-56-0 C22H22F3N 357.41
VX-765 273404-37-8 C24H33ClN4O6 509.0
11

Route of Synthesis

12

References

[1]. Canalejo et al (2000) The in vitro effect of calcitriol on parathyroid cell proliferation and apoptosis. J.Am.Soc.Nephrol. 11 1865. Beer and Myrthue (2004)

[2]. Calcitriol in cancer treatment: from the lab to the clinic. Mol.Cancer Ther. 3 373.

[3]. Nijenhuis et al (2006) The novel vitamin D analog ZK191784 as an intestine-specific vitamin D antagonist. FASEB J. 20 1589.

[4]. L. F. HILL , C. J. VAN DEN BERG & E. B. MAWER.Vitamin D Metabolism in Experimental Uraemia: Effects on Intestinal Transport 45Ca and on Formation of 1,25-Dihydroxycholecalciferol in Rat. nature new biology 232, 189-191

[5]. Anthony W. Norman, James F. Myrtle, Ronald J, et al. 1,25-Dihydroxycholecalciferol: Identification of the Proposed Active Form of Vitamin D3 in the Intestine. Science 2 July 1971: Vol. 173 no. 3991 pp. 51-54

[6]. M. R. Haussler, D. W. Boyce, E. T. Littledike, et al. A Rapidly Acting Metabolite of Vitamin D3. PNAS January 1, 1971 vol. 68 no. 1 177-181

[7]. James F. Myrtle, Mark R. Haussler, Anthony W. Norman. Evidence for the Biologically Active Form of Cholecalciferol in the Intestine. Evidence for the Biologically Active Form of Cholecalciferol in the Intestine. March 10, 1970 The Journal of Biological Chemistry, 245, 1190-1196.

[8]. L. G. Raisz, C. L. Trummel, M. F. Holick, H. F. Deluca. 1,25-Dihydroxycholecalciferol: A Potent Stimulator of Bone Resorption in Tissue Culture. Science 18 February 1972: Vol. 175 no. 4023 pp. 768-769.

[9]. Krishnan AV, Swami S, Feldman D.Equivalent anticancer activities of dietary vitamin D and calcitriol in an animal model of breast cancer: Importance of mammary CYP27B1 for treatment and prevention.J Steroid Biochem Mol Biol. 2012 Aug 23.

[10]. Alkharfy KM, Al-Daghri NM, Yakout SM, Ahmed M.Calcitriol Attenuates Weight-Related Systemic Inflammation and Ultrastructural Changes of the Liver in a Rodent Model.Basic Clin Pharmacol Toxicol. 2012 Aug 21.

Protocol Reference

13

More Information

Calcitriol

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